反応 #737231

反応方程式

ethyl bromoacetate

ethyl 7-nitro-1H-indole-2-carboxylate

sodium hydride

→

ethyl 1-ethoxycarbonylmethyl-7-nitro-1H-indole-2-carboxylate

収率 78.0%

溶媒

N,N-dimethylformamide

反応条件

後処理

1. 1
   workup.STIRRINGthe resulting mixture was stirred at 50-60° C. for 4 hours
2. 2
   温度The reaction mixture was cooled to room temperature
3. 3
   抽出followed by extraction with ethyl acetate (three times)
4. 4
   洗浄The organic layer was washed with water
5. 5
   乾燥dried over anhydrous magnesium sulfate
6. 6
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
7. 7
   その他the resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=5/95)

実験手順

To a solution of ethyl 7-nitro-1H-indole-2-carboxylate (2.00 g, 8.45 mmol) in N,N-dimethylformamide (50 ml) was added 60% sodium hydride (0.34 g, 8.54 mmol), and the reaction mixture was stirred at room temperature until it became transparent. Then, ethyl bromoacetate (1.43 g, 8.54 mmol) was added and the resulting mixture was stirred at 50-60° C. for 4 hours. The reaction mixture was cooled to room temperature and poured into ice water, followed by extraction with ethyl acetate (three times). The organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=5/95) to obtain ethyl 1-ethoxycarbonylmethyl-7-nitro-1H-indole-2-carboxylate (2.11 g).

出典